I had to think about this because there are a fair number I watch with regularity, for various reasons.
-LOTR is an absolute masterpiece. It's been a part of my life, through the books initially, and then the films, since I was born. Peter Jackson captured the spirit of it all so well, and every piece of it, from a storytelling perspective, to a cinematography perspective, to acting, to sets, to screenwriting, all of it is incredible. I don't go home for Thanksgiving very often anymore because I'm too poor to do that and a December trip, and since all of my friends and arguewithatree do go home, I'm usually alone. So I take two days, sit down with a feast for one, crank the volume, and watch all of the director's cuts in one sitting, and the next day follow it with the Godfather. So that's frequently watched and a tradition. I'll end up viewing it a number of times throughout the year too.
-Sam Mendes' Away We Go is well up there as well. I have a very close, personal, intimate relationship with this film with two people. It's "our" film between arguewithatree and myself, the one that we feel sappy about and love watching and identify with, minus the baby aspect. Fuck babies. And my best friend, jackdanielswife (you won't find anything there. She's too busy to ever make her way to this site grrr), because it was the film we watched where we realized we are absolutely in love with each other... but it's not quite romantic. It's different. Something about that film made us realize it, over a year after we broke up. It makes it an important film because those are the two most important people in my world that I would do anything for, so to think about them every time I watch it and how much I love them makes it an invaluable experience.
-The Royal Tenenbaums and The Life Aquatic with Steve Zissou. These have a wild variety of associations for me personally, and Royal is also associated with jackdanielswife. We likened ourselves to Margot and Ritchie, but more than that, I just find them enjoyable, in all their over the top style and sappiness. As much of a monstrous film buff as I am, as much as I'll sit down and bore someone with diatribes about how important Bela Tarr or Ingmar Bergman are, as much as I drop ridiculous money on restored versions of Kurasawa and Orson Welles films with extras, and Criterion versions, I'll never get on board with my other film buffs who love to hate on Wes Anderson. He 's populist and enjoyable. There's nothing wrong with it and I'll revel in it.
-But the one I've probably seen the most without reason, without personal ties or celebrations or planned holidays, just something that I pop in to watch every so often for the hell of it? Galaxy Quest. Galaxy Quest is the perfect film. How many years has it been since it was released? It's just as hilarious. It's just as beautifully tongue in cheek. It's perfectly self-deprecating. It's just as fun. All of it makes for that at any time, any place, any mood, I can watch that and be into it.